How do i get my grid to stay on top of plane
First solution : Use X-Ray Mode
The shortcut is ALT + Z or click this icon in the top right : 
Second solution : Use the material alpha
This works only in lookdev mode and you need to set Eeevee as your renderer first. Click on your object and go to its material or add one if it doesn't have one already. Then go the alpha value and lower it, don't forget to set the alpha blend mode to &quot;Alpha Blend&quot;.

Enhance the grid line visibility
If you want to see the grid lines more easily, you can tweak the opacity inside the user preferences :